


Dating Blues

by EddieFook



Series: Quickie!verse [19]
Category: Supernatural
Genre: Awkward Flirting, Destiel - Freeform, Fluff, Humor, M/M, Mentions of Smut, Terrible dates, at least they tried, really terrible dates
Language: English
Status: Completed
Published: 2017-02-05
Updated: 2017-02-05
Packaged: 2018-09-22 07:36:48
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,695
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9592076
Author URL: https://archiveofourown.org/users/EddieFook/pseuds/EddieFook
Summary: Dating can be hard. Like really hard. Especially if you're Dean Winchester who wants to plan the perfect, memorable date for the man he has incredible chemistry with. And these dates are memorable, just maybe not in the way Dean wishes.





	

**Author's Note:**

> Yeah this one is totally short...ish

Dean was going to refuse to give up. They’d been on four dates and he had utterly ruined his chances with Cas. He was so incredibly gone on Cas, the man was hot as the sun, funny, and Dean could feel the potential of something so deep and good that Dean just couldn’t give up. Cas had the potential of being Dean’s best friend and forever person, that chemistry was totally there.

They had met at the library. Dean was up on a ladder grabbing a book on philosophy when this sweater vest under a mop of unruly hair walked past him. And for the love of all dignity Dean slipped on the ladder. Cas took pity on him, mainly also because he felt that chemistry at first sight, and took him to coffee and they had a great time. So of course they were eager to try dating. Which…well…

If he could just figure out how to properly fucking date that would be fantastic.

Maybe if he went over all the dates he would find the answer to his issues.

**Date One**

“It’s ok, I didn’t expect you to know I couldn’t cook.”

“That was far from cooking, that was a massacre, how do you even survive?” Dean joked and felt his stomach drop slightly at the look on Cas’s face.

“Yes, of course, well I suppose it is unusual for a man my age not to be able to cook.” Cas fiddled with the stain on his shirt and Dean felt like the world’s largest idiot.

“Hey, no it’s fine, there’s a ton of shit I can’t do,” but it sounded hollow in his mouth. “So, um, can I make an ass of myself again and ask for another date?”

“You want to?” Cas looked up, shocked. They had spent the night picking at one another from the way Cas cut the onions to how Dean didn’t clean up after himself. To everyone else it looked like the worst first date in history.

And then Cas spilled hot spaghetti sauce all over his shirt.

And Dean had…laughed.

He did feel bad about that, and he apologized immediately and he was not going to be surprised in the slightest if Cas said he didn’t want another date.

“I’m free on Friday night,” Cas said quickly almost surprising himself.

“Ok, I’ll pick you up?” Cas nodded and they had to walk close to get between their cars. Dean turned his face and Cas was leaning forward and Dean thought _hey kiss, bit surprising but yeah I’ll take it_ , and went in and kissed.

Well what Cas was leaning in for was a hand shake but Dean had leaned in and Cas backed away so fast he fell onto his car and the alarm went off.

“I, um, shit,” Dean turned crimson and jumped into his car and sped away.

**Date Two**

“Wow, again something…different.” Cas had a timid smile and Dean grinned.

“Yeah, me and my brother went here all the time when we were younger.” Dean grinned, they got out of the car and the familiar sounds of screams and creaking machines and the smells of fried food drifted toward them. “I hope you like roller coasters,” his grin was innocent and large it got Cas to smile at that alone.

“Well I have never attended an amusement park so I will trust in you.” Dean looked shocked but at least this time he could keep his foot out of his mouth.

“We need to get you some carny food.”

Remembering the date it was probably them around the table with a plethora of deep fried food around them that got Cas to say yes to another date. Because around the table was fun. They laughed and ate too much and felt that chemistry that was forgotten during their last date.

Which of course was ruined when Cas almost threw up on Dean after their very first ride.

They were able to make it to a bathroom where Dean worried himself to near tears hearing Cas retching in the bathroom.

“I am so sorry,” Dean held out his hands uselessly to help Cas in any way. “Is there…”

“I think I should go home,” Cas was sweaty and trembling and looked incredibly green.

“Yeah, of course, I’ll take you home now. I’m sorry I forgot you haven’t been on a rollercoaster and all that food….”

“Dean,” Cas smiled weakly and looped his arm in Dean’s. “It’s fine. How about I plan the next date?” Dean brightened.

“Are you serious?”

“Do you not want a date?” Dean helped Cas in the car. “I wouldn’t be surprised if you didn’t, I vomited on our second date.”

“No! I mean yeah! I want another date, you can plan whatever I’ll do anything. Obviously I’m really bad at planning dates.”

Cas didn’t talk much as soon as Dean started driving, he looked incredibly queasy and Dean apologized about eight more times. There was no mistaken kiss at the end of the night but Dean did awkwardly pat Cas on the shoulder as the man got out of the car.

**Date Three**

“Yeah, Cas I totally dig…wine…” Dean grinned but it wasn’t as big or as bright as before the amusement park.

“This is just an informal tasting and then whatever we like we will give our order to the restaurant and they’ll make a meal around that wine.” Cas was excited, he’d originally was going to go with his friend Meg, but he wanted to go with someone he was actually attracted to. 

“Ok, I’m up for anything new,” Dean shrugged and followed Cas along.

And by new it was a bunch of swigging in glasses and pretending he could taste the nuttiness or mineral Cas was excited about. Dean drank whatever was put in front of him in large gulps and didn’t notice the disdainful looks on the other guests. Cas didn’t seem to mind and did mention Dean could use a spit cup but that just grossed Dean out.

And after twenty wines Dean was pleasantly buzzed.

“I liked the Bordeaux, how about you?” Dean cocked his head.

“Was that the red one, like the really red one that even tasted a bit red?” he blushed when he heard sniggers from the couple next to them.

“Yes,” Cas grinned, “That’s how I would describe the Bordeaux.” He nodded and Dean felt a little better.

They put their order in and waited at the bar with full glasses of a white wine that Cas picked and eating cheese and figs. Again the conversation flowed and they laughed and felt a deep chemistry.

Dinner was incredible, Dean made a joke about being happy there weren’t any tiny portions which Cas heartily agreed. They enjoyed the surf and turf with large glasses of the red Bordeaux and Dean felt a warm haze settle on the world.

The next course brought rich chocolate, caramel cake and deep globes of port.

“I can understand why we took a cab here,” Dean swayed and Cas grinned woozily at him. Dean had enjoyed the port so much they ordered a dark chocolate and cherry tort with another vintage. Cas’s cheeks had a flush and Dean’s were full on roses.

“Right,” Cas grinned, “You’re hot, like disgustingly, superstar hot. What’s it like to be so hot?”

“Look in the mirror buddy I think you’ll get your answer,” Dean drunkenly leaned in and tweaked Cas’s nose.

Which, _naturally_ , led to their tongues down each other’s throat.

Obviously.

***

When Dean woke the next morning he was alone. He was also naked and covered with about two orgasms worth of dried cum. Disgusted with himself he immediately went to shower and tried to remember what the hell he and Cas got up to. The last thing he remembered was that incredible kiss in the back of the cab and then now.

Well, maybe the next time he and Cas rolled in the hay he’d actually have the joy of remembering it.

**Date Four**

So Dean wasn’t going to admit that he was a little pissed. Was sleeping with him so terrible that Cas never wanted to mention it again? Or not even acknowledge Dean other than asking for a fourth date? Like Dean knew he didn’t rock worlds when he was drunk but he’d never had complaints before.

Dean decided boring and straightforward had to work so he planned dinner and a movie. They would do the movie first and then dinner and it had to work.

Cas was running late so Dean bought the movie tickets and waited by the door for him.

“Hey! Work was crazy,” Cas leaned in and kissed chastely and grinned. Dean was a bit frosty because come on, was the sex that bad that Cas was just going to ignore that it even happened? And of course it was Dean’s failings, because look at Cas, so it must have been so terribly horrible that Cas was just going to never mention it again. Which really put a damper in Dean’s ego because he was kind of hoping for more sex in the future.

They found seats and settled as Cas chatted away about his work. Dean tried to listen and be happy that he and Cas were actually having a good time, but he couldn’t get the lack of care on Cas’s part out of his head.

Dean was already planning not asking for a fifth date by the time the opening credits rolled and he was grateful because it gave him an excuse not to listen to Cas’s wonderfulness and complete lack of remembering Dean’s nakedness.

That was until the first death. Dean hadn’t forgotten Cas next to him but it wasn’t until about twenty minutes in (this was a real slasher) when the first person died, Dean looked over at Cas.

And the dude looked terrified.

He had his hands up covering his eyes and his body was trying to get in a fetal position. Dean took pity on the guy and lifted up the armrest between them and opened his arm up. Cas surged in and trembled against Dean’s chest for the remainder of the movie. And even though he didn’t want to, he really didn’t, Dean very much enjoyed Cas’s warmth against his chest and the dude’s scent was incredible.

“Sorry I should have asked you if you wanted to see this…” Dean’s voice died as they walked out of the theatre and Cas shrugged. He had grabbed Dean’s hand in the last twenty minutes of the movie and hadn’t let it go since.

“That’s fine, I enjoyed cuddling with you,” Cas winked and Dean remembered again why he was so pissed.

“Oh yeah, ok, so you liked it in a movie theatre but not in my house. Ok good to note.” Dean said it before he even thought and Cas froze.

“What?”

“The night of our last date, you…well you…we…”

“Kissed…” Cas helped.

“Yeah and then we went back to my place…” Dean took in the confused look on Cas’s face. “We did go back to my place, didn’t we?” Cas shook his head slowly.

“We made out and then the cabbie yelled at us and dropped me off at my place. You said you were a lady and wanted to keep me out of your pants for another date, that you wanted to play hard to get.”

“But I…I woke up covered in…”

“Covered in what?” Cas smirked and Dean realized that what Cas was saying was true. He hadn’t slept with Cas and he had treated Cas so terribly tonight…

“I’m so sorry!” He moaned and scrubbed his hand over his face.

“You seem to be saying that a lot on our dates,” Cas mused, he had a wide smile on his face and Dean couldn’t help but match it. “Take me out to dinner and we’ll plan a fifth date.”

It was the best date they’d ever had. They went to a simple diner and they laughed so much and forgot all the terribleness of their previous dates.

“Dude I don’t think I should be trusted to plan the next date…” Dean eyed Cas warily as the man sipped from his strawberry milkshake.

“Hey we’re here aren’t we? If you were that terrible we wouldn’t still be dating,” Cas stole the cherry off the top of Dean’s sundae. “And I don’t know about you but I’ve been having fun with you and they are definitely memorable.” Dean laughed.

“Ok, I’ll make it memorable.”

**Date Five**

And boy it was.

Dean picked Cas up and drove to a paint your own pottery store. Hey Cas had said memorable. And it was unusual and Dean hoped that they were going to have fun. Dean was not wrong.

When Cas saw the store he folded in half and cried he was laughing so hard.

“Well, it’s memorable,” Cas wiped his eyes and Dean felt a spark of something small in his stomach.

“And let me guess, no artistic abilities whatsoever?”

“None at all,” Cas grinned.

“Me too,” Dean winked and they both walked into the pottery place. They both chose plates and they both agreed not to look at the other’s until they were done. The employees tried to help as much as possible but there was no way that Dean and Cas could be helped. Then it was just to babysit them to make sure they didn’t paint penises or some other vulgarity.

After an hour they swapped plates and Dean couldn’t breathe he was laughing so hard.

“Well this is tropical,” Cas looked benignly at Dean who started crying even harder. Dean reached around and flipped the plate so it was upside down and the palm tree with the fronds and coconuts became something else entirely. “Oh that’s much better.”

Cas hadn’t even tried to be subtle.

It was a cock.

And it was hard.

And it said _tonight_ under it.

“Self portrait?” Dean held the plate up to his face and Cas laughed.

“Mm either mine or yours, I don’t care.” Cas leaned over the table and kissed Dean softly. “You want to come to my place? I can cook.” Dean nodded and Cas beamed slowly.

They paid for their plates, Cas had to pay extra for his profanity but the dude hardly cared. He just shrugged and laid out the cash and grabbed Dean’s hand.

***

“Holy,” Dean blinked, “Holy shit,” he could barely blink let alone pant, let alone pet all over Cas’s back. He did try the last but it was more of just awkward patting on random parts of Cas’s naked skin. “I don’t think I’ve ever had sex like that before.” 

“Thanks,” Cas’s ruffled head popped up from the pillow next to Dean’s head. Dean was on his back and Cas on his stomach with his limbs flopped over Dean’s chest and legs. “I’ll take that as a compliment, though I think you helped greatly.”

“Yeah, I guess,” Dean groaned when he shifted around. That had been fucking _spectacular_ sex and Dean wasn’t ready to leave Cas’s bed any time. “We should have just fallen into bed before the first date.”

“Mmmm then we wouldn’t have had all those terrible dates,” Cas hummed.

“Cas,” Dean brushed his fingers through sweaty, chocolate hair. “I know I didn’t…I know I was really shit at planning these dates…but…um…”

“Dean we just had amazing sex, you can talk around me.”

“I’m sorry I was so terrible but if I promise never to plan anything again can we still date?”

“Only if you promise that if we get to it we’ll have a really terrible wedding.” Cas rolled and snuggled in even deeper, “We can have awful food, and the cake can be a mess, and we’ll drop our rings, and our photographer will be drunk.”

“You’re on.”

***

“These are terrible!” Cas laughed himself giddy.

“It was your idea to have a drunk photographer,” Dean laughed with him.

“Well, we are nothing but memorable,” Cas kissed his brand new husband and they both grinned.


End file.
